Light-Promoted Nickel-Catalyzed C-O/C-N Coupling of Aryl Halides with Carboxylic Acids and Sulfonamides

被引:22
作者
Zhao, Tian-Tian [1 ]
Qin, Hao-Ni [1 ]
Xu, Peng-Fei [1 ,2 ]
机构
[1] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
[2] Lanzhou Univ, Chinese Acad Agr Sci, Lanzhou Vet Res Inst, Coll Vet Med,State Key Lab Vet Etiol Biol, Lanzhou 730000, Peoples R China
关键词
PHOTOREDOX; MECHANISMS; GENERATION; ROUTES; MILD;
D O I
10.1021/acs.orglett.2c04210
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A general strategy for the construction of dual-functional carbon- heteroatom bonds has been developed via a light-promoted nickel catalytic system. Employing a simple NiBr2 as the catalyst without any exogeneous ligands and photosensitizers, a variety of esters and sulfonamide N-arylation derivatives, including celecoxib-and glimepiride-derived sulfonamides, were readily accessed with high functional group tolerance and high efficiency. Moreover, the UV-vis absorption spectrum and free radical trapping experiments aimed at revealing the mechanism of the reaction are also presented.
引用
收藏
页码:636 / 641
页数:6
相关论文
共 50 条
[1]  
Abe K., 2013, J COMPUT CHEM JPN, V12, P168, DOI [10.2477/jccj.2013-0003, DOI 10.2477/JCCJ.2013-0003]
[2]   Analysis of Past and Present Synthetic Methodologies on Medicinal Chemistry: Where Have All the New Reactions Gone? [J].
Brow, Dean G. ;
Bostrom, Jonas .
JOURNAL OF MEDICINAL CHEMISTRY, 2016, 59 (10) :4443-4458
[3]   A Unified Approach to Decarboxylative Halogenation of (Hetero)aryl Carboxylic Acids [J].
Chen, Tiffany Q. ;
Pedersen, P. Scott ;
Dow, Nathan W. ;
Fayad, Remi ;
Hauke, Cory E. ;
Rosko, Michael C. ;
Danilov, Evgeny O. ;
Blakemore, David C. ;
Dechert-Schmitt, Anne-Marie ;
Knauber, Thomas ;
Castellano, Felix N. ;
MacMillan, David W. C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (18) :8296-8305
[4]   Aryl amination using ligand-free Ni(II) salts and photoredox catalysis [J].
Corcoran, Emily B. ;
Pirnot, Michael T. ;
Lin, Shishi ;
Dreher, Spencer D. ;
DiRocco, Daniel A. ;
Davies, Ian W. ;
Buchwald, Stephen L. ;
MacMillan, David W. C. .
SCIENCE, 2016, 353 (6296) :279-283
[5]   A Survey of the Structures of US FDA Approved Combination Drugs [J].
Das, Pradipta ;
Delost, Michael D. ;
Qureshi, Munaum H. ;
Smith, David T. ;
Njardarson, Jon T. .
JOURNAL OF MEDICINAL CHEMISTRY, 2019, 62 (09) :4265-4311
[6]   Transition Metal-Catalyzed Dicarbofunctionalization of Unactivated Olefins [J].
Dhungana, Roshan K. ;
Shekhar, K. C. ;
Basnet, Prakash ;
Giri, Ramesh .
CHEMICAL RECORD, 2018, 18 (09) :1314-1340
[7]   Mechanisms of Nickel-Catalyzed Coupling Reactions and Applications in Alkene Functionalization [J].
Diccianni, Justin ;
Lin, Qiao ;
Diao, Tianning .
ACCOUNTS OF CHEMICAL RESEARCH, 2020, 53 (04) :906-919
[8]   A nickel(II) coordination polymer derived from a tridentate Schiff base ligand with N,O-donor groups: synthesis, crystal structure, spectroscopy, electrochemical behavior and electrocatalytic activity for H2O2 electroreduction in alkaline medium [J].
dos Santos, Rachel Dias ;
Freire dos Santos, Sinara de Fatima ;
Moura, Fagner da Silva ;
Sousa Maia, Paulo Jose ;
da Fonseca, Bruna Teixeira ;
de Almeida Santos, Regina Helena ;
Medeiros, Marta Eloisa ;
dos Santos Garrido, Francisco Manoel ;
Casellato, Annelise .
TRANSITION METAL CHEMISTRY, 2017, 42 (04) :301-310
[9]   Photoredox-Catalyzed Hydrocarboxymethylation of Alkenes [J].
Fang, Jie ;
Hu, Qiang ;
Dong, Wan-Li ;
Xu, Guo-Qiang ;
Hu, Xiu-Qin ;
Luo, Yong-Chun ;
Xu, Peng-Fei .
CCS CHEMISTRY, 2021, 3 (10) :95-104
[10]   The 25th Anniversary of the Buchwald-Hartwig Amination: Development, Applications, and Outlook [J].
Forero-Cortes, Paola A. ;
Haydl, Alexander M. .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2019, 23 (08) :1478-1483